Kid-friendly holiday rentals in Sheboygan

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Sheboygan family-friendly rentals

Kid-friendly house rentals

Superhost
Home in Sheboygan
4.76 out of 5 average rating, 21 reviews

Modern 5 Bedroom Getaway House

JanetRating, 5 stars7 months ago
Location was perfect for what we had on our plans. I would definitely recommend BookWorm Gardens. My grandchildren enjoyed the variety of games provided.
Top guest favourite
Home in Sheboygan
4.99 out of 5 average rating, 132 reviews

2 Min Walk to Food, 15 to Pier! 4 Bedrooms 2K/2Q

RicciRating, 5 stars6 months ago
This is the second time I stayed at Chelsea’s house. It is the perfect location for the beach, the river and the downtown Sheboygan area and also super close to Kohler for the spa and food and wine festival! Perfect cozy home for a girls trip or a family get away!
Guest favourite
Home in New Holstein
4.86 out of 5 average rating, 139 reviews

Growe's Guest House - just like Grandma's!

Israel IzzyRating, 5 stars6 months ago
The place was clean, nice and good amenities. Mary was responsive to our questions and very helpful. We were there for the SCCA Championship races at Road America ! We Left at 7am and returned at 10pm everyday. We did enjoy it. We only wish the upstairs bathroom had a shower instead of a soaking tub. (Since 4 guys all trying to take a shower before rushing off to sleep. Very nice place.
Top guest favourite
Home in Glenbeulah
4.98 out of 5 average rating, 125 reviews

Stay at Sunrise LLC, Like being at Grandma's

DavidRating, 5 stars6 months ago
This place is suitable for a small family or a few adults. Very clean and well thought-out amenities made it quite attractive. Because we were very busy at Road America every day, we did not have an opportunity to use the kitchen except to make coffee, but had we wanted to cook, I'm sure we would have found everything needed. The only "warning" is that anyone with some mobility issues might find the stairway to the second floor a bit daunting. If we need a place in the area again, we would likely choose this house again.
Top guest favourite
Home in Sheboygan
4.95 out of 5 average rating, 42 reviews

Wander Back Inn to Sheboygan

LaurieRating, 5 stars1 month ago
We had a great time at this place. Everything was as described. Very easy to work with and accommodating.
Guest favourite
Home in Sheboygan
4.96 out of 5 average rating, 225 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

DebbieRating, 5 stars1 week ago
This place was just what our family needed. It was wonderful to bring our dog Annabelle and explore the Sheboygan area. We used the coffee bar and did the wine exchange and the place felt like "home"! I would highly recommend for a home like atmosphere and spending quality time together. We hope to visit again when the weather is warm to swim in what looks like beautiful beaches. Thank you for your hospitality!
Top guest favourite
Home in Sheboygan
5 out of 5 average rating, 27 reviews

Private 3 bd country home 2 miles N of Kohler WI

JanetRating, 5 stars7 months ago
The perfect location and house for our visit to Wisconsin for a wedding! We loved the house, it had everything we needed for our stay. Coming from a rural area the location made us feel like being at home. The grandkids enjoyed the backyard, complete with games for them to play and room to run. There was plenty of room and seating outside to sit back and enjoy the cooler weather and sunrise. Shelly was quick to respond to questions and was a great host. If ever back in Wisconsin would definitely stay here again!
Top guest favourite
Home in Plymouth
4.96 out of 5 average rating, 297 reviews

Country Cheese Factory - King Bed!

HeatherRating, 5 stars2 weeks ago
Wonderful location, comfortable beds, plenty of room for all of us, and beautiful surroundings. We really enjoyed our stay and look forward to coming back.

Family-friendly apartment rentals

Top guest favourite
Flat in Waldo
4.98 out of 5 average rating, 278 reviews

The Blue Cobb House

MikeRating, 5 stars2 days ago
My wife and I were celebrating our 45th Wedding Anniversary- Jewel made it so special for us! And her place? WOW! We’ve stayed in AirBnb’s from Olympia to Siesta Key, from Zagreb to Dubrovnik- and Jewel’s place and her hospitality outshines them all! Beautiful accommodations, spotless, every possible provision, comfortable and supportive bed, - it was simply heavenly!!! Thanks to Jewel!!!
Superhost
Flat in Plymouth
4.64 out of 5 average rating, 300 reviews

Pineyard Plymouth Apartment

CynthiaRating, 5 stars2 weeks ago
This was our second stay at Kerry's place. It was exactly what we needed, the price is right, the flat is clean and well-appointed, and the beds are comfy. All-in-all a lovely overnight experience.
Guest favourite
Flat in Sheboygan
4.84 out of 5 average rating, 25 reviews

2BR Apt Near Beach & Downtown

DillonRating, 5 stars3 days ago
Hosts were great. Place was clean! Great first experience using Air B&B would definitely stay again!
Guest favourite
Flat in Elkhart Lake
4.96 out of 5 average rating, 142 reviews

Schoolhouse Straight Inn

CandyRating, 5 stars1 day ago
We needed a dog friendly place for a Road America weekend. This was great. I walked the dog nearby and across the road to a beautiful lakefront neighborhood. Didn’t cook there but heated up takeout food. Cute backyard that was too wet for us to hang out in. Comfy beds and cool race memorabilia in unit.
Top guest favourite
Flat in Sheboygan
4.97 out of 5 average rating, 158 reviews

Modern Upstairs Apt - Steps from Lake Michigan

SamRating, 5 stars1 week ago
Michelle's place has great access to the Bay area and greatly renovated. The primary bedroom with bath is gorgeous especially with heated tile floor. The second bedroom was a bit small but it was also comfortable. The second bath was behind the kitchen so the couple who used the second bedroom has to walk through the living room and the kitchen but it was not a big deal. We felt the coffee table in the living room was a bit small for four of us but again not a big deal at all. One thing we have noticed was the linen are high quality! And we paid the great price probably because it is early (water in Michigan lake was still pretty cold). Neighborhood restaurants were great and kitchen has all the tools and dishes for our first night dinner. We wished that we had access to outdoor grill but maybe it will be available during the summer. Great stay in small coastal town in WI. Highly recommended!
Guest favourite
Flat in Sheboygan
4.89 out of 5 average rating, 9 reviews

Parkside Studio Apartment

TomRating, 5 stars3 days ago
Ashlynn was very kind and helpful. We arrived late at somehow the code wasn’t working for us but thankfully she was alerted to it and was able to assist. I felt badly about waking her up but she was so kind about it. The place was beautiful and bed was great. If in the area definitely a great spot to stay.
Top guest favourite
Flat in Sheboygan
4.98 out of 5 average rating, 139 reviews

Lovely modern two bedroom home with fire pit

LeaRating, 5 stars1 week ago
We had an amazing stay!!! Ellen was extremely friendly, welcoming and made you feel right at home. The place was in spotless condition and it’s very apparent the owner takes top notch care of the unit! The unit was actually much larger and spacious compared to what I was expecting. Everything you need for a comfortable stay.. and more! You will not be disappointed with anything in this rental, that’s a guarantee!! Thank you, Ellen!
Guest favourite
Flat in Sheboygan
4.92 out of 5 average rating, 66 reviews

Entire Upper Rental Unit-South Central Sheboygan

EricaRating, 5 stars6 months ago
The apartment was easy to get to, very clean, and in a great location in town. Sarah was very responsive and helpful.

Family-friendly apartment rentals

Top guest favourite
Apartment in Sheboygan
4.97 out of 5 average rating, 65 reviews

Urban Townhouse

HalieRating, 5 stars1 month ago
this was the perfect place for our stay. we wanted a condo with a hot tub so we could relax and hang out. our plan was to spend a good amount of time hanging out and chilling at the BNB, and just go to a couple different places around Sheboygan. this condo was perfect for that. I have no complaints, this place was perfect. if I ever return to Sheboygan, we'll definitely be looking to stay here again.
Top guest favourite
Apartment in Sheboygan
4.98 out of 5 average rating, 41 reviews

A Glorious Getaway Sheboygan - LUX Lake Condo

JohnRating, 5 stars1 month ago
Susan was exceptionally responsive and inviting. She let us arrive early for our Mother's celebration of life weekend. It was easy to find once you figured out the address and unit numbers. Parking was ideal and plentiful. You can see the beach and lake from the walk out balcony.
Apartment in Sheboygan
4.79 out of 5 average rating, 14 reviews

Modern South Pier Condo on Sheboygan River!

LauraRating, 5 stars4 months ago
Nice, comfortable condo. Easy parking, elevator, cozy.
Guest favourite
Apartment in Sheboygan
4.97 out of 5 average rating, 31 reviews

Heavenly Condo in the Malibu of the Midwest

LisaRating, 5 stars2 months ago
Debbie was super responsive from day 1 onward. Really enjoyed working with her for our 6-day stay. The place was nice and warm despite the sub-zero temps we had when there. Bed was comfortable and lots of hot water for showers. New appliances so meals in were easy. All in all a great place to stay. Thank you Debbie.
Top guest favourite
Apartment in Sheboygan
4.93 out of 5 average rating, 40 reviews

Ellis District Urban Lake Condo

ChristyRating, 5 stars2 weeks ago
Sara was very responsive accommodating for our needs. The space itself was spacious for the size, the kitchen was well equipped with any cooking you may do, tons of towels and travel size toiletries in vase you forgot something walking distance to the marina was a nice option, however it was a tad nippy so I chose to stay inside while my husband and son were in the airspft event. will definitely stay again!
Top guest favourite
Apartment in Sheboygan
4.97 out of 5 average rating, 37 reviews

Beach condo for 12: 4 bdrms, 2+ baths, treadmill

KateRating, 5 stars2 weeks ago
We booked this condo for a girls' weekend / reading retreat. The condo was huge, the kitchen was well stocked, and there was plenty of space to spread out. Sheboygan is an adorable town, and the view of the beach was gorgeous even if the weather wasn't quite warm enough to get out there and enjoy it.
Guest favourite
Apartment in Sheboygan
4.93 out of 5 average rating, 86 reviews

Janelle's Dockside Condo

ElaineRating, 5 stars3 weeks ago
We loved everything about this stay. Janelle has created a very beautiful space with absolutely everything we needed for a peaceful vacation. It is spacious and immaculately clean. The location is priceless. We had an easy walk to Lake Michigan, great restaurants, fun shops, and great coffee. We will definitely be back!
Top guest favourite
Apartment in Elkhart Lake
5 out of 5 average rating, 28 reviews

Car Condo Rental in Elkhart Lake

AaronRating, 5 stars6 months ago
We loved how it was decorated and it had everything we needed even a wine bottle opener! Also it is right down the road from Road America. We will definitely be staying here again!

Quick stats about holiday rentals that are kid-friendly in Sheboygan

  • Total rentals

    80 properties

  • Nightly prices starting at

    £30 before taxes and fees

  • Total number of reviews

    4.6K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

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